Condensation product of the anthraquinone series and process of making same



Patented Jan. 5, 1926.

UNITED STATES PAUL SCHETELIG, OF BASEL, SWITZERLAND, ASSIGNOR TO 'THE FTRM SOCIETY OF PATENT -.OFFICE.

CHEMICAL INDUSTRY IN BASLE. OF BASEL, SWITZERLAND.

CONDENSATION PRODUCT OF THE ANTI-IRAQUINONE SERIES AND PROCESS OF MAKING SAME.

Ho Drawing.

T 0 all whom it may concern:

Be 1t known that I, PAUL ScHn'rrLIo, a citizen of Switzerland, residing at Basel,

Switzerland, have invented ncwand useful Condensation Products of the Anthraquinone Series and Processes of Making Same,

ofwhich the following is a full, clear, and

' ries, the amino group of which may also be mono-substituted, with derivatives of 1.3.5-

triazine halogenated'in the nucleus, as for instance cyanuric chloride. There are'thus obtained valuable condensation products containing 1.3.5-triazine nuclei which may be used partly as colouring matters, partly as starting materials for the production of dyestuffs;

As a result of further study and experiment on the lines of the above cited fundamental process, I have found that valuable new products are obtained by causing nucleal halogen derivatives of the 1.3.5-

triazine to react on compounds of the general formula:

wherein one of the letters a stands for an amino group and the other for a hydrogen atom and, in some cases, condensing the products thus obtained, which may still con- Application filed May 4, 1925. serial No. 2s,o2i.

tain mobile halogen atoms, with suitable substances, as for example, amino compounds.

There are thus obtained dyestuffs of the general formula I) i wherein one of the two lettersb stands for a' radical N 7 0 C-z i i v I IH wherein one of the letters a stands for an amino group and the other for a hydrogen atom, employed as intermediate products for the manufacture of the dyestuffs of the present invention are obtainable by the action of 5- or 8-amino-1-chloro-anthraquinone on anthranilic acid and subsequent condensation of the l-anthraquinone anthranilic acid thus obtained with aid of a suitable condensing agent such as sulfuric acid or chlorosulfonic acid. The 5- or 8-amino-2.l-anthraquinone acridones form red to violet needles, soluble in concentrated sulfuric acid to an orange toyelloW-orange solution and yielding a violet vat with hydrosulfite and caustic soda solution. The 8-amino-4-chloro-2.l-

a thraquinone acridone obtained in similar manner from l-amrno-fi-chloro-Q;-benzo1c acid shows analogous properties.

The following examples illustrate the invention, the parts being by weight:

Example 34 parts of 8-amino-2.l-anthraquinoneacridone are introduced into 800 parts of nitrobenzene and 9.3 pants of cyanuric chloride are added. The mixture is heated gradually, while stirring, to 190-200" C. and stirring is continued at this temperature for some hours. The liquid is cooled and filtered and the solid matter is washed with nitroh'enzene and alcohol and dried. The new condensation product is a dark violetpowder, soluble in concentrated sulfuric acid to a red-orange solution and yielding with 'hydrosulfite and caustic soda solution a violet-hrown vat in. which cotton is dyed a red-violet of good fastness to light, washing and chlorine. The corresponding dyestufi' from 4-21minol-ch1oro-2.1-anthraquinone-acridone shows analogous properties. If the 5-amino-2.1-anthraquinone-acridone be substituted for the 8-derivative there is obtained a dyestufi which roduces on cotton very fast brownish hordeaux tints.

Example 2.

24 parts of the condensation product from one molecular proportion of cyanuric chloride and one molecular proportion of tamino- 2.Lanthraquinone-acridone are' mixed with 17 parts of 5-amino-2.1-anthraquinone-acridone and 500 parts of nitrobenzene; the mixture is boiled for a long time in a reflux apparatus. The cooled liquid is then filtered and the solid matter washed, with nitrohenzene and alchohol and dried.- Thisnew condensation product is a, dark powder, soluble in concentrated sulfuric acid to a redorange solution, and yielding with hydro- -sulfite and caustic soda solution, a dark red" violet vat which dyes cotton fast violet-grey tints.

mouse? wherein one of the letters a stands for the amino group and the other for a hydrogen atom.

2. The herein described process for the manufacture of condensation products of the anthraquinone series by causing nucleal halogen derivatives of the 1,3.5-triazine to react on compounds of the general formula H l l wherein one of the letters a stands for the amino group and the other for a hydrogen atom and condensing the resulting reaction products with further compounds which have reactive hydrogen atoms.

3. The herein described process for the manufacture of condensation products 015-" the anthraquinoneseries by causing one molecule of cyanuric chloride-to react on one molecule of a compound of the general formula wherein one ofthe letters a stands for the amino group and the other for a hydrogen .tion product with one molecule of the same compound 'ofthe above sp'ecified general formula.

4. As new products the herein described condensation products'of the general formula 3] and a being substituents of which one at least is an amino radical which maybe substituted, and wherein the other letter 6 stands for a hydrogen atom, which products form dark powders, soluble in concentrated sulfuric acid to a red-orange and inalkaline properties hydro'sulfite solution to a Violet-brown solution, dyeing cotton tints which vary from red-violet to bordeaux and grey of excellent of fastness.

5. As new products the herein described condensation products of the mula wherein one of the two letters 6 is a radical V wherein one of the twoletters b is a radical wherein one of the two letters 6 1s a radical general foris linked to the cyanuric nucleus, whic lution, dyein cotton tints which Vary from red-violet to ordcaux and grey of excellent properties of fastness.

6. As new products the herein described conldensation products of the general formu a far.

y and a being subst-itucnts of which one at least is'an arylamino radical which contains an anthraquinone nucleus, and wherein the other letter 1) stands for a hydrogen atom, which products form dark powders, soluble in concentrated sulfuric acid to a red orange and in alkaline hydrosulfite solution to a, violet-brown solution, dyeing cotton tints which vary from red-violet to bordeaux and grey of excellent properties of fastness.

7. As new products the herein described condensation products of the symmetrical general formula wherein the two Rs each mean a. compound of the general formula in which one of the letters a stands for a other for a hydrogen NH-group and the the'NH-grou atom and in which compound products form dark powders, soluble'in conccntrated sulfuric acid to a red-orange solution and in an alkaline hydrosulfite solution to a; violet-brown solution, dyeing cotton r'ed- 10. Material dyed with the dyestuffs of violet'to brownish bordeaux tints of excellent claim 6.

properties of fastness. "11. Material dyed with the dyest ufi's of w 8. Material dyed with the dyestufis of claim 7. f 5 claim 4. In witness whereof I have hereunto signed 9. Material dyed with the dyestuffs of my name this 22nd day of April 1925. I claim 5. I PAUL SCHETELIG. 

